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I5400 Sigma-Aldrich

Indole-5-carboxylic acid

99%

Synonym: 5-Carboxyindole

  • CAS Number 1670-81-1

  • Empirical Formula (Hill Notation) C9H7NO2

  • Molecular Weight 161.16

  •  Beilstein/REAXYS Number 124391

  •  EC Number 216-799-6

  •  MDL number MFCD00005678

  •  PubChem Substance ID 24896068

  •  NACRES NA.22

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Properties

Related Categories Building Blocks, C7 to C9, Chemical Synthesis, Heterocyclic Building Blocks, Indoles More...
Quality Level   100
assay   99%
mp   211-213 °C (lit.)
SMILES string   OC(=O)c1ccc2[nH]ccc2c1
InChI   1S/C9H7NO2/c11-9(12)7-1-2-8-6(5-7)3-4-10-8/h1-5,10H,(H,11,12)
InChI key   IENZCGNHSIMFJE-UHFFFAOYSA-N

Description

General description

Indole-5-carboxylic acid is an indole derivative. On electropolymerization, it affords electroactive polymer film of poly(indole-5-carboxylic-acid). Different concentrations of indole-5-carboxylic acid in sulfuric acid solution has been investigated for the preventive action against mild steel corrosion. On electropolymerization it affords a trimeric product. Characterization studies of the trimeric product by 1H NMR and various one- and two-dimensional NMR techniques have been reported.

Application

• Reactant for preparation of tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles, as potential anticancer immunomodulators
• Reactant for preparation of indolyl-quinolines via metal- and solvent-free autoxidative coupling reaction
• Reactant for preparation of anthranilic acids using bromamine-B oxidant and palladium chloride catalyst
• Reactant for synthesis of indirubin derivatives
• Reactant for preparation of amide conjugates with ketoprofen, as inhibitors of Gli1-mediated transcription in Hedgehog pathway
• Reactant for preparation of piperazine-bisamide analogs as human growth hormone secretagogue receptor antagonists for treatment of obesity

Indole-5-carboxylic acid is the suitable reagent used to study the intramolecular excited state proton transfer in indole-2-carboxylic acid and indole-5-carboxylic acid in various solvents in acidic, basic, and neutral media by steady state and time resolved fluorescence spectroscopy. It may be used in the electrochemical synthesis of poly(indole-5-carboxylic acid) (PICA) films.

Packaging

1, 5 g in poly bottle

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles
Peer-Reviewed Papers
15

References

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